IP Library › Granted Patent US 8,686,131

Granted Patent B2

US 8,686,131 · App. 13/326,060 · Granted Apr 1, 2014

Synthetic heparin trisaccharides

Inventors: Joachim Seifert (Forest Lake, AU); Latika Singh (Forest Lake, AU); Tracie E. Ramsdale (Sunnybank, AU); Michael L. West (Birkdale, AU); Nicholas B. Drinnan (Highgate Hill, AU)

Assignee: Alchemia Limited

C07H13/04 C07H13/08 C07H15/18 C07H15/10

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Quick Facts

Patent No.: US 8,686,131
App. No.: 13/326,060
Granted: Apr 1, 2014
Kind: B2

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Abstract

Preparation and use of synthetic trisaccharides useful for the preparation of synthetic heparinoids.

Claims (208)

1. A trisaccharide building block of General Formula XXIII,

wherein:

X 2 is selected from the group consisting of a hydroxyl group; thioalkyl, thioaryl, halogen, trichloroacetimidoyl, and a t butyldiphenylsilyloxy; and wherein the stereochemistry may be alpha or beta;

R P1 is selected from the group consisting of 4-methoxyphenyl, benzyl, substituted benzyl groups, alkylacyl, arylacyl and alkylarylacyl, or substituted alkylacyl, arylacyl and alkylarylacyl protecting groups, and carbonate protecting groups;

R P2 is selected from the group consisting of alkylacyl, arylacyl and alkylarylacyl, or substituted alkylacyl, arylacyl and alkylarylacyl protecting groups, carbonate protecting groups, silyl protecting groups, carbamate protecting groups, and C 3 -C 5 alkenyl;

R E1 is selected from the group consisting of methyl, C 2 -C 5 alkyl, substituted alkyl, C 3 -C 5 alkenyl, benzyl and substituted benzyl groups;

R B1 is selected from the group consisting of an azido function, an amine, an NH-Dde and NH-DTPM group, or R H2 and R B1 can combine together to form a cyclic carbamate;

R H is selected from the group consisting of benzyl or substituted benzyl protecting group, allyl, and allyloxycarbonyl;

R H2 is selected from the group consisting of benzyl or substituted benzyl protecting group, allyl, and allyloxycarbonyl, or R H2 and R B1 independently can combine together to form a cyclic carbamate;

R S5 is selected from the group consisting of 4-methoxyphenyl, substituted benzyl groups, alkylacyl, arylacyl or alkylarylacyl, and substituted alkylacyl, arylacyl or alkylarylacyl protecting groups; carbonate protecting groups, a t butyldiphenylsilyl, allyl, methoxymethyl, methoxyethyl, and benzyloxymethyl; or R S5 and R H can be combined to form a cyclic acetal or ketal moiety;

R S3 is selected from the group consisting of 4-methoxyphenyl, substituted benzyl groups, alkylacyl, arylacyl or alkylarylacyl, and substituted alkylacyl, arylacyl or alkylarylacyl protecting groups, carbonate protecting groups, a t butyldiphenylsilyl or other such substituted silyl protecting group, allyl, methoxymethyl, methoxyethyl, and benzyloxymethyl;

R S4 is selected from the group consisting of 4-methoxyphenyl, substituted benzyl groups, alkylacyl, arylacyl or alkylarylacyl, and substituted alkylacyl, arylacyl or alkylarylacyl protecting groups, carbonate protecting groups, a t butyldiphenylsilyl, allyl, methoxymethyl, methoxyethyl, and benzyloxymethyl; or R S4 and R B may be combined to form a cyclic carbamate; and,

R B is selected from the group consisting of an azido function, an amine, an NH-Dde and an NH-DTPM group, or R S4 and R B can combine together to form a cyclic carbamate.

2. The trisaccharide building block of claim 1 ,

wherein:

X 2 is selected from the group consisting of a hydroxyl group, thioalkyl, thioaryl, chloro, fluoro, trichloroacetimidoyl, and a t butyldiphenylsilyloxy; and wherein the stereochemistry may be alpha or beta;

R S3 is selected from the group consisting of 4-methoxyphenyl, substituted benzyl groups, alkylacyl, arylacyl or alkylarylacyl, and substituted alkylacyl, arylacyl or alkylarylacyl protecting groups; carbonate protecting groups, and tert-Butyldiphenylsilyl;

R S4 is selected from the group consisting of 4-methoxyphenyl, substituted benzyl groups, alkylacyl, arylacyl or alkylarylacyl, and substituted alkylacyl, arylacyl or alkylarylacyl protecting groups, carbonate protecting groups, and tert-Butyldiphenylsilyl, or R S4 and R B may be combined to form a cyclic carbamate;

R P2 is selected from the group consisting of alkylacyl, arylacyl and alkylarylacyl, or substituted alkylacyl, arylacyl and alkylarylacyl protecting groups, and allyloxycarbonyl;

R P1 is selected from the group consisting of 4-methoxyphenyl, benzyl; substituted benzyl groups, alkylacyl, arylacyl and alkylarylacyl, or substituted alkylacyl, arylacyl and alkylarylacyl protecting groups, and allyloxycarbonyl;

R E1 is selected from the group consisting of methyl, C 2 -C 5 alkyl, substituted alkyl, benzyl, and substituted benzyl groups;

R H2 is selected from the group consisting of benzyl or substituted benzyl protecting group, or R H2 and R B1 independently can combine together to form a cyclic carbamate;

R H is selected from the group consisting of benzyl or substituted benzyl protecting group; and,

3. The trisaccharide building block of claim 2 , wherein:

X 2 is selected from a hydroxyl group, thioalkyl, thioaryl, chloro, fluoro, trichloroacetimidoyl, and a t butyldiphenylsilyloxy; and wherein the stereochemistry may be alpha or beta;

R P2 is selected from the group consisting of alkylacyl, arylacyl and alkylarylacyl, or substituted alkylacyl, arylacyl and alkylarylacyl protecting groups, and allyloxycarbonyl;

R H2 is selected from the group consisting of benzyl or substituted benzyl protecting group;

and,

R S5 is selected from the group consisting of alkylacyl, arylacyl or alkylarylacyl, and substituted alkylacyl, arylacyl or alkylarylacyl protecting groups, carbonate protecting groups, and tert-butyldiphenylsilyl.

4. The trisaccharide building block of claim 1 , wherein:

R S4 is selected from the group consisting of 4-methoxyphenyl, substituted benzyl groups, alkylacyl, arylacyl or alkylarylacyl, and substituted alkylacyl, arylacyl or alkylarylacyl protecting groups, carbonate protecting groups, and tert-Butyldiphenylsilyl, or R S4 and R B may be combined to form a cyclic carbamate;

R B is selected from the group consisting of an azido function, an amine, or R S4 and R B can combine together to form a cyclic carbamate;

X 2 is selected from the group consisting of a thiomethyl, thioethyl, thiophenyl, thiocresyl, trichloroacetimidoyl, and tert-butyldiphenylsilyloxy, and wherein the stereochemistry may be alpha or beta;

R E1 is selected from the group consisting of methyl, allyl, and benzyl;

R P1 is benzyl;

R P2 is selected from the group consisting of benzoate, and allyloxycarbonyl;

R H is benzyl;

R H2 is benzyl;

R S5 is selected from the group consisting of 4-methoxyphenyl, 4-methoxybenzyl, benzoyl, and tert-butyldiphenylsilyl; and,

R B1 is selected from the group consisting of an azido function, or R H2 and R B1 can combine together to form a cyclic carbamate.

5. A trisaccharide building block of General Formula XXIV,

wherein:

X 1 is selected from the group consisting of hydroxy, methoxy, thiomethyl, thioethyl, thiocresyl, trichloroacetimidoyl, a t butyldiphenylsilyloxy, and a lipoaminoacid, and wherein the stereochemistry may be alpha or beta;

R H and R H1 are independently selected from a benzyl or substituted benzyl protecting group, or R H1 and R A can combine together to form a cyclic carbamate;

R A is an azido, or R H1 and R A can combine together to form a cyclic carbamate;

R S1 , R S2 , R S3 and R S4 are independently selected from the group consisting of: 4-methoxyphenyl; benzoyl, or R S4 and R B may be combined to form a cyclic carbamate;

R E2 is selected from the group consisting of methyl, allyl, benzyl, and substituted benzyl groups; and,

R B is an azido function, or R S4 and R B can combine together to form a cyclic carbamate; and,

R L is selected from a H atom; a levulinoyl, chloroacetyl, 4-acetoxybenzoyl, 4-acetamidobenzoyl, 4-azidobenzoyl, a benzyl group, a 4-acetoxybenzyl, 4-acetamidobenzyl, γ-aminobutyryl, 4-N-[1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethylamino]-butyryl, 4-N-[1-(1,3-dimethyl-2,4,6(1H,3H,5H)-trioxopyrimidin-5-ylidene)methylamino]-butyryl, 4-N-Alloc-butyryl, 4-N-Fmoc-butyryl, 4-N-Boc-butyryl, allyloxycarbonyl, allyl ether, and carbonate protecting groups.

6. A trisaccharide building block of General Formula XXIII,

wherein:

X 2 is selected from the group consisting of a hydroxyl group, thioalkyl, thioaryl, fluoro, trichloroacetimidoyl, and t butyldiphenylsilyloxy, and wherein the stereochemistry may be alpha or beta;

R P1 is selected from the group consisting of 4-methoxyphenyl, benzyl, a substituted benzyl group, and a carbonate protecting group;

R P2 is selected from the group consisting of 4-methoxyphenyl, benzyl, a substituted benzyl group, an alkylacyl, arylacyl, or alkylarylacyl, or substituted alkylacyl, arylacyl and alkylarylacyl protecting group, a carbonate protecting group, a silyl protecting group, a carbamate protecting group, and C 3 -C 5 alkenyl;

R E1 is selected from the group consisting of methyl, C 2 -C 5 alkyl, substituted C 2 -C 5 alkyl, C 3 -C 5 alkenyl, benzyl, and a substituted benzyl group;

R B1 is selected from the group consisting of an azido function, an amine, and an NH-Dde and an NH-DTPM group; or R H2 and R B1 can combine together to form a cyclic carbamate;

R H is selected from the group consisting of benzyl, a substituted benzyl protecting group, allyl, and allyloxycarbonyl;

R H2 is selected from the group consisting of benzyl, a substituted benzyl protecting group, allyl, allyloxycarbonyl; or R H2 and R B1 independently can combine together to form a cyclic carbamate;

R S5 is selected from the group consisting of 4-methoxyphenyl, 4-methoxybenzyl, a substituted benzyl group, benzoyl, 4-chlorobenzoyl, arylacyl, alkylarylacyl, allyloxycarbonyl, ethoxycarbonyl, tertbutoxycarbonyl, a carbonate protecting group, a t butyldiphenylsilyl protecting group, allyl, methoxymethyl, methoxyethyl, and benzyloxymethyl; or R S5 and R H can be combined to form a cyclic acetal or ketal moiety;

R S3 is selected from the group consisting of 4-methoxyphenyl, a substituted benzyl group, an arylacyl, alkylarylacyl, or substituted alkylacyl, arylacyl, or alkylarylacy protecting group; a carbonate protecting group, a t butyldiphenylsilyl, allyl, methoxymethyl, methoxyethyl, and benzyloxymethyl;

R S4 is selected from the group consisting of 4-methoxyphenyl, a substituted benzyl group, arylacyl or alkylarylacyl, or substituted alkylacyl, arylacyl, or alkylarylacyl protecting group, a carbonate protecting group, a t butyldiphenylsilyl, allyl, methoxymethyl, methoxyethyl, and benzyloxymethyl; or R S4 and R B may be combined to form a cyclic carbamate; and,

R B is selected from the group consisting of an azido function, an amine, an NH-Dde and an NH-DTPM group; or R S4 and R B can combine together to form a cyclic carbamate.

7. The trisaccharide building block of claim 6 ,

wherein:

X 2 is selected from the group consisting of a hydroxyl group, thioalkyl, thioaryl, fluoro, trichloroacetimidoyl, and a t butyldiphenylsilyloxy; and wherein the stereochemistry may be alpha or beta;

R S3 is selected from the group consisting of 4-methoxyphenyl, a substituted benzyl group, an arylacyl or alkylarylacyl, or substituted arylacyl or alkylarylacyl protecting group, a carbonate protecting group, and tert-Butyldiphenylsilyl;

R S4 is selected from the group consisting of 4-methoxyphenyl, a substituted benzyl group, an arylacyl or alkylarylacyl, or substituted arylacyl or alkylarylacyl protecting group, a carbonate protecting group, and tert-Butyldiphenylsilyl; or R S4 and R B may be combined to form a cyclic carbamate;

R B is selected from the group consisting of an azido function, an amine, an NH-Dde and an NH-DTPM group; or R S4 and R B can combine together to form a cyclic carbamate;

R P2 is selected from the group consisting of 4-methoxyphenyl, benzyl, a substituted benzyl group, an alkylacyl, arylacyl, or alkylarylacyl, or substituted alkylacyl, arylacyl, or alkylarylacyl protecting group, and a carbonate protecting group;

R P1 is selected from the group consisting of 4-methoxyphenyl, benzyl, a substituted benzyl group, and a carbonate protecting group;

R E1 is selected from the group consisting of methyl, C 2 -C 5 alkyl, substituted C 2 -C 5 alkyl, benzyl, and a substituted benzyl group;

R B1 is selected from the group consisting of an azido function, an amine, an NH-Dde and an NH-DTPM group; or R H2 and R B1 can combine together to form a cyclic carbamate;

R H2 is selected from the group consisting of benzyl, a substituted benzyl protecting group; or R H2 and R B1 independently can combine together to form a cyclic carbamate;

R H is selected from the group consisting of benzyl and a substituted benzyl protecting group; and,

8. The trisaccharide building block of claim 6 ,

wherein:

X 2 is selected from the group consisting of a hydroxyl group, thioalkyl, thioaryl, fluoro, trichloroacetimidoyl, and a t butyldiphenylsilyloxy; and wherein the stereochemistry may be alpha or beta;

R S3 is selected from the group consisting of 4-methoxyphenyl, a substituted benzyl group, an arylacyl or alkylarylacyl, or substituted arylacyl or alkylarylacy protecting group, a carbonate protecting group, and tert-Butyldiphenylsilyl;

R B is selected from the group consisting of an azido function, an amine, an NH-Dde and an NH-DTPM group; or R S4 and R B can combine together to form a cyclic carbamate;

R P2 is selected from the group consisting of 4-methoxyphenyl, benzyl, a substituted benzyl group, an alkylacyl, arylacyl, or alkylarylacyl, or substituted alkylacyl, arylacyl, or alkylarylacyl protecting group, and a carbonate protecting group;

R P1 is selected from the group consisting of 4-methoxyphenyl, benzyl, a substituted benzyl group, and a carbonate protecting group;

R E1 is selected from the group consisting of methyl, C 2 -C 5 alkyl, substituted alkyl, benzyl, and a substituted benzyl group;

R B1 is selected from the group consisting of an azido function, an amine, an NH-Dde and an NH-DTPM group; or R H2 and R B1 can combine together to form a cyclic carbamate;

R H2 is selected from the group consisting of benzyl and a substituted benzyl protecting group; or R H2 and R B1 independently can combine together to form a cyclic carbamate;

R H is selected from the group consisting of benzyl and a substituted benzyl protecting group; and,

R S5 is selected from the group consisting of 4-methoxyphenyl, a substituted benzyl group, an arylacyl or alkylarylacyl, or substituted arylacyl or alkylarylacy protecting group, a carbonate protecting groups, and tert-butyldiphenylsilyl.

9. The trisaccharide building block of claim 6 ,

wherein:

R S3 is selected from the group consisting of 4-methoxyphenyl, a substituted benzyl group, an alkylacyl, arylacyl, or alkylarylacyl, or substituted alkylacyl, arylacyl or alkylarylacyl protecting group, and tert-butyldiphenylsilyl;

R S4 is selected from the group consisting of 4-methoxyphenyl, a substituted benzyl group, an alkylacyl, arylacyl, or alkylarylacyl, or substituted alkylacyl, arylacyl, or alkylarylacyl protecting group, a carbonate protecting group, and tert-Butyldiphenylsilyl; or R S4 and R B may be combined to form a cyclic carbamate;

R B is selected from the group consisting of an azido function and an amine; or R S4 and R B can combine together to form a cyclic carbamate;

X 2 is selected from the group consisting of thiomethyl, thioethyl, thiophenyl, thiocresyl, trichloroacetimidoyl, and tert-butyldiphenylsilyloxy; and wherein the stereochemistry may be alpha or beta;

R E1 is selected from the group consisting of methyl, allyl, and benzyl;

R P1 is benzyl;

R P2 is selected from the group consisting of benzyl, benzoate, and allyloxycarbonyl;

R H is benzyl;

R H2 is benzyl;

R S5 is selected from the group consisting of 4-methoxyphenyl, 4-methoxybenzyl, benzoyl, and t butyldiphenylsilyl; and,

R B1 is an azido function; or R H2 and R B1 can combine together to form a cyclic carbamate.

10. A trisaccharide represented by formula XXVIII:

wherein

X is independently for each occurrence selected from the group consisting of hydroxyl, silyloxy, halide, alkylthio, arylthio and —OC(NH)CCl 3 ;

R is independently for each occurrence selected from the group consisting of aryl, arylalkyl, silyl, acyl and alkenyloxycarbonyl; and

R′ is independently for each occurrence selected from the group consisting of alkyl, aryl and arylalkyl; and,

R″ is selected from the group consisting of aryl, silyl, acyl and alkenyloxycarbonyl.

11. A trisaccharide represented by Formula XXXII:

12. A trisaccharide represented by Formula XXXIII:

13. A trisaccharide represented by Formula XXXIV:

14. A trisaccharide represented by Formula XXXV:

15. A trisaccharide represented by the formula,

wherein:

X 2 is selected from the group consisting of thiomethyl, thioethyl, thiophenyl, thiocresyl, trichloroacetimidoyl, and tert-butyldiphenylsilyloxy; and wherein the stereochemistry may be alpha or beta.

16. A trisaccharide building block of General Formula XXIII,

wherein:

X 2 is selected from the group consisting of a hydroxyl group; thioalkyl, thioaryl, halogen, trichloroacetimidoyl, and a t butyldiphenylsilyloxy; and wherein the stereochemistry may be alpha or beta;

R P2 is selected from the group consisting of 4-methoxyphenyl, benzyl, substituted benzyl and a silyl protecting group;

R E1 is selected from the group consisting of methyl, C 2 -C 5 alkyl, substituted alkyl, C 3 -C 5 alkenyl, benzyl and substituted benzyl groups;

R B1 is selected from the group consisting of an azido function, an amine, an NH-Dde and NH-DTPM group, or R H2 and R B1 can combine together to form a cyclic carbamate;

R H is selected from the group consisting of benzyl or substituted benzyl protecting group, allyl, and allyloxycarbonyl;

R S3 is selected from the group consisting of 4-methoxyphenyl, substituted benzyl groups, arylacyl or alkylarylacyl, and substituted arylacyl or alkylarylacyl protecting groups, a t-butyldiphenylsilyl allyl, methoxymethyl, methoxyethyl, and benzyloxymethyl;

R S4 is selected from the group consisting of 4-methoxyphenyl, substituted benzyl groups, alkylacyl, arylacyl or alkylarylacyl, and substituted alkylacyl, arylacyl or alkylarylacyl protecting groups, carbonate protecting groups, a t-butyldiphenylsilyl, allyl, methoxymethyl, methoxyethyl, and benzyloxymethyl; and,

R B is selected from the group consisting of an azido function, an amine, an NH-Dde and an NH-DTPM group, or R S4 and R B can combine together to form a cyclic carbamate.

17. The trisaccharide building block of claim 16 ,

wherein:

R E1 is selected from the group consisting of methyl, C 2 -C 5 alkyl, substituted alkyl, benzyl, and substituted benzyl groups;

R H2 is selected from the group consisting of benzyl or substituted benzyl protecting group, or R H2 and R B1 independently can combine together to form a cyclic carbamate;

R H is selected from the group consisting of benzyl or substituted benzyl protecting group; and,

18. The trisaccharide building block of claim 17 ,

wherein:

X 2 is selected from a hydroxyl group, thioalkyl, thioaryl, chloro, fluoro, trichloroacetimidoyl, and a t butyldiphenylsilyloxy; and wherein the stereochemistry may be alpha or beta;

R E1 is selected from the group consisting of methyl, C 2 -C 5 alkyl, substituted C 2 -C 5 alkyl, benzyl, and substituted benzyl groups;

R H2 is selected from the group consisting of benzyl or substituted benzyl protecting group, or R H2 and R B1 independently can combine together to form a cyclic carbamate;

R H is selected from the group consisting of benzyl or substituted benzyl protecting group; and,

19. The trisaccharide building block of claim 16 ,

wherein:

R B is selected from the group consisting of an azido function, an amine, or R S4 and R B can combine together to form a cyclic carbamate;

X 2 is selected from the group consisting of a thiomethyl, thioethyl, thiophenyl, thiocresyl, trichloroacetimidoyl, and t-butyldiphenylsilyloxy, and wherein the stereochemistry may be alpha or beta;

R E1 is selected from the group consisting of methyl, allyl, and benzyl;

R P1 is benzyl;

R H is benzyl;

R H2 is benzyl;

R S5 is selected from the group consisting of 4-methoxyphenyl, 4-methoxybenzyl, benzoyl, and t-butyldiphenylsilyl; and,

R B1 is selected from the group consisting of an azido function, or R H2 and R B1 can combine together to form a cyclic carbamate.

20. A trisaccharide building block of General Formula XXIII,

wherein:

X 2 is selected from the group consisting of a hydroxyl group; thioalkyl, thioaryl, halogen, trichloroacetimidoyl, and a t butyldiphenylsilyloxy; and wherein the stereochemistry may be alpha or beta;

R P2 is selected from the group consisting of 4-methoxyphenyl, benzyl, substituted benzyl and a silyl protecting group;

R E1 is selected from the group consisting of methyl, C 2 -C 5 alkyl, substituted alkyl, C 3 -C 5 alkenyl, benzyl and substituted benzyl groups;

R B1 is selected from the group consisting of an azido function, an amine, an NH-Dde and NH-DTPM group, or R H2 and R B1 can combine together to form a cyclic carbamate;

R H is selected from the group consisting of benzyl or substituted benzyl protecting group, allyl, and allyloxycarbonyl;

R S3 is selected from the group consisting of 4-methoxyphenyl, substituted benzyl groups, alkylacyl, arylacyl or alkylarylacyl, and substituted alkylacyl, arylacyl or alkylarylacyl protecting groups, carbonate protecting groups, a t-butyldiphenylsilyl, allyl, methoxymethyl, methoxyethyl, and benzyloxymethyl;

R S4 is selected from the group consisting of 4-methoxyphenyl, substituted benzyl groups, arylacyl or alkylarylacyl, and substituted arylacyl or alkylarylacyl protecting groups, a t-butyldiphenylsilyl allyl, methoxymethyl, methoxyethyl, and benzyloxymethyl; and,

R B is selected from the group consisting of an azido function, an amine, an NH-Dde and an NH-DTPM group, or R S4 and R B can combine together to form a cyclic carbamate.

21. The trisaccharide building block of claim 20 ,

wherein:

R E1 is selected from the group consisting of methyl, C 2 -C 5 alkyl, substituted alkyl, benzyl, and substituted benzyl groups;

R H2 is selected from the group consisting of benzyl or substituted benzyl protecting group, or R H2 and R B1 independently can combine together to form a cyclic carbamate;

R H is selected from the group consisting of benzyl or substituted benzyl protecting group; and,

22. The trisaccharide building block of claim 20 ,

wherein:

X 2 is selected from a hydroxyl group, thioalkyl, thioaryl, chloro, fluoro, trichloroacetimidoyl, and a t butyldiphenylsilyloxy; and wherein the stereochemistry may be alpha or beta;

R E1 is selected from the group consisting of methyl, C 2 -C 5 alkyl, substituted C 2 -C 5 alkyl, benzyl, and substituted benzyl groups;

R H2 is selected from the group consisting of benzyl or substituted benzyl protecting group, or R H2 and R B1 independently can combine together to form a cyclic carbamate;

R H is selected from the group consisting of benzyl or substituted benzyl protecting group; and,

23. The trisaccharide building block of claim 20 ,

wherein:

R B is selected from the group consisting of an azido function, an amine, or R S4 and R B can combine together to form a cyclic carbamate;

X 2 is selected from the group consisting of a thiomethyl, thioethyl, thiophenyl, thiocresyl, trichloroacetimidoyl, and t-butyldiphenylsilyloxy, and wherein the stereochemistry may be alpha or beta;

R E1 is selected from the group consisting of methyl, allyl, and benzyl;

R P1 is benzyl;

R H is benzyl;

R H2 is benzyl;

R S5 is selected from the group consisting of 4-methoxyphenyl, 4-methoxybenzyl, benzoyl, and t-butyldiphenylsilyl; and,

R B1 is selected from the group consisting of an azido function, or R H2 and R B1 can combine together to form a cyclic carbamate.

Assignments (3)

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 18, 2015

From: ALCHEMIA LIMITED ACN 071 666 334

To: DR. REDDY'S LABORATORIES, SA

Reel/Frame 037077/0141 →

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 7, 2012

From: SEIFERT, JOACHIM; SINGH, LATIKA; RAMSDALE, TRACIE ELIZABETH; WEST, MICHAEL LEO; DRINNAN, NICHOLAS BARRY

To: ALCHEMIA PTY LTD.

Reel/Frame 027822/0852 →

CHANGE OF NAME Recorded Mar 7, 2012

From: ALCHEMIA PTY LTD.

To: ALCHEMIA LIMITED

Reel/Frame 027831/0034 →

Priority Claims (1)

AU 7587 · Sep 7, 2001 · national

Continuity (3)

Division 12354643 · Jan 15, 2009

Division 10488677

Related Publication 20120208993A1 · Aug 16, 2012